7-hydroxy-8-methoxyflavone

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 黄酮类化合物
• 英文名称: 7-hydroxy-8-methoxyflavone
• 英文别名: 7-Hydroxy-8-methoxy-2-phenylchromen-4-one；7-hydroxy-8-methoxy-2-phenylchromen-4-one
• 化学式: C₁₆H₁₂O₄
• 分子量: 268.269
• InChiKey: DEEUASFOBQPPHH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  55.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  7,8-二甲氧基黄酮 在 Aspergillus flavus ATCC₉₁₇₀ 作用下， 以36%的产率得到7-hydroxy-8-methoxyflavone
  参考文献：
  名称：

  Microbial metabolism. Part 10: Metabolites of 7,8-dimethoxyflavone and 5-methoxyflavone

  摘要：

  Microbial transformation of 7,8-dimethoxyflavone (1) by Mucor ramannianus produced five metabolites: 7,8-dimethoxy-4'-hydroxyflavone (2), 3',4'-dihydroxy-7,8-dimethoxyflavone (3), 7,3'-dihydroxy-8-methoxyflavone (4), 7,4'-dihydroxy-8-methoxyflavone (5) and 8-methoxy-7,3',4'-trihydroxyflavone (6). It was, however, completely converted to a single metabolite, 7-hydroxy-8-methoxyflavone (7) by Aspergillus flavus. 5-Methoxyflavone (8), when fermented with Beauveria bassiana, gave a single product, 5-methoxyflavanone (9). Conversion of 8 with Aspergillus alliaceus yielded the metabolite 4'-hydroxy-5-methoxyflavone (10). The structures of the compounds 2-7, 9 and 10 were established by spectroscopic methods.

  DOI：

  10.1080/14786410902829797

文献信息

• O-methylation of flavonoids by cell-free extracts of calamondin orange
  作者：Gunter Brunet、Ragai K. Ibrahim

  DOI：10.1016/0031-9422(80)85102-8

  日期：——

  hydroxyls of a number of flavonoids, indicating the existence in citrus tissues of ortho, meta, para and 3-O-methyltransferases. The latter, hitherto unreported enzyme, catalysed the formation of 3-O-methyl ethers of galangin and quercetin. The stepwise O-methylation of a number of compounds, especially quercetin and quercetagetin, tends to suggest a coordinated sequence of O-methylations on the surface

  摘要 柑桔（Citrus mitis）的无细胞提取物催化了许多类黄酮的几乎所有羟基的O-甲基化，表明柑橘组织中存在邻位、间位、对位和3-O-甲基转移酶。后者，迄今未报道的酶，催化高良姜素和槲皮素的 3-O-甲基醚的形成。许多化合物的逐步 O-甲基化，尤其是槲皮素和槲皮素，往往表明多酶复合物表面上存在协调的 O-甲基化序列。所使用的类黄酮底物的甲基受体能力与它们的羟基取代模式和它们的负电子密度分布有关。
• Characterization of two candidate flavone 8-O-methyltransferases suggests the existence of two potential routes to nevadensin in sweet basil
  作者：Anna Berim、David R. Gang

  DOI：10.1016/j.phytochem.2013.05.001

  日期：2013.8

  recombinant protein was found to be active with a wide range of o-diphenols, and methylated the 8-OH moiety of the flavone backbone with higher catalytic efficiency than the 3'-OH group of candidate substrates. To further investigate flavone 8-O-methylation, the activity of a putative cation-independent flavonoid 8-O-methyltransferase from the same EST collection was assessed with available substrate analogs

  区域选择性 6-,7-,8-,3'- 和 4'-O-甲基化是甜罗勒 (Ocimum basilicum L.) 毛状体中产生的亲脂性黄酮结构多样性的基础。位置 6、7 和 4' 被最近描述的一组不依赖阳离子的酶甲基化。阳离子依赖性 O-甲基转移酶的作用仍需要阐明。在这里，罗勒毛状体 EST 数据库用于识别可能接受类黄酮作为底物的依赖于 Mg(2+) 的 O-甲基转移酶。发现重组蛋白对广泛的邻二酚具有活性，并且以比候选底物的 3'-OH 基团更高的催化效率甲基化黄酮骨架的 8-OH 部分。为了进一步研究黄酮 8-O-甲基化，使用可用的底物类似物评估来自同一 EST 集合的推定的阳离子非依赖性类黄酮 8-O-甲基转移酶的活性。值得注意的是，它被其预期产品之一的栀子 B 强烈抑制。所研究的两种蛋白质的催化能力表明，可能存在两种替代内瓦登辛（一些罗勒栽培品种中的主要黄酮）的途径。将潜在基因的表达与
• METHOD OF MANUFACTURING METHOXY-ISOFLAVONES BY BIOTRANSFORMATION AND USE THEREOF
  申请人：NATIONAL UNIVERSITY OF TAINAN

  公开号：US20170198318A1

  公开（公告）日：2017-07-13

  A method of manufacturing methoxy-isoflavones by biotransformation and a use thereof are revealed herein. The method comprises the steps of synthesizing a nucleic acid sequence including a SpOMT2884 gene ofStreptomyces peucetius ; cloning the nucleic acid sequence into an expression vector to form a cyclic recombinant plasmid; transforming the cyclic recombinant plasmid into a microbial expression system ( Escherichia coli ); and incubating the microbial expression system in a medium containing 8-hydroxydaidzeins therein for generating methoxy-isoflavones.
• Microbial metabolism. Part 10: Metabolites of 7,8-dimethoxyflavone and 5-methoxyflavone
  作者：Wimal Herath、Julie Rakel Mikell、Ikhlas Ahmad Khan

  DOI：10.1080/14786410902829797

  日期：2009.9.10

  Microbial transformation of 7,8-dimethoxyflavone (1) by Mucor ramannianus produced five metabolites: 7,8-dimethoxy-4'-hydroxyflavone (2), 3',4'-dihydroxy-7,8-dimethoxyflavone (3), 7,3'-dihydroxy-8-methoxyflavone (4), 7,4'-dihydroxy-8-methoxyflavone (5) and 8-methoxy-7,3',4'-trihydroxyflavone (6). It was, however, completely converted to a single metabolite, 7-hydroxy-8-methoxyflavone (7) by Aspergillus flavus. 5-Methoxyflavone (8), when fermented with Beauveria bassiana, gave a single product, 5-methoxyflavanone (9). Conversion of 8 with Aspergillus alliaceus yielded the metabolite 4'-hydroxy-5-methoxyflavone (10). The structures of the compounds 2-7, 9 and 10 were established by spectroscopic methods.